Synthesis, structures, and photophysical properties of π-expanded oligothiophene 8-mers and their Saturn-like C₆₀ complexes.
Identifieur interne : 001328 ( PubMed/Checkpoint ); précédent : 001327; suivant : 001329Synthesis, structures, and photophysical properties of π-expanded oligothiophene 8-mers and their Saturn-like C₆₀ complexes.
Auteurs : Hideyuki Shimizu [Japon] ; José D. Cojal González ; Masashi Hasegawa [Japon] ; Tohru Nishinaga [Japon] ; Tahmina Haque [Japon] ; Masayoshi Takase [Japon] ; Hiroyuki Otani [Japon] ; Jürgen P. Rabe ; Masahiko Iyoda [Japon]Source :
- Journal of the American Chemical Society [ 1520-5126 ] ; 2015.
Abstract
Two isomers of a multifunctional π-expanded macrocyclic oligothiophene 8-mer, E,E-1 and Z,Z-1, were synthesized using a McMurry coupling of a dialdehyde composed of four 2,5-thienylene and three ethynylene units under high dilution conditions. On the other hand, cyclo[8](2,5-thienylene-ethynylene) 2 was synthesized by intramolecular Sonogashira cyclization of ethynyl bromide 5. From STM measurements, both E,E-1 and Z,Z-1 formed self-assembled monolayers at the solid-liquid interface to produce porous networks, and from X-ray analyses of E,E-1 and 2, both compounds had a round shape with a honeycomb stacked structure. E,E-1 formed various fibrous polymorphs due to nanophase separation of the macrorings. E,E-1 and Z,Z-1 in solution exhibited photochromism upon irradiation with visible and UV light, respectively, and this photoisomerization was confirmed by using STM. Furthermore, amorphous films of Z,Z-1 and E,E-1 showed photoisomerization, although single crystals, fibers, and square tubes of E,E-1 remained unchanged under similar conditions. E,E-1 with a 12.5-14.7 Å inner cavity incorporated fullerene C60 in the cavity in solution and the solid state to produce a Saturn-like complex, whose structure was determined by X-ray analysis. 2 also formed a Saturn-like complex with C60 in the solid state. These Saturn-like complexes are stabilized by van der Waals interactions between the sulfur atoms of 8-mer and C60. The complexes exhibited charge-transfer interactions in the solid state. Like E,E-1, Saturn-like complex E,E-1⊃C60 formed small cube and fiber structures depending on the solvent used, whereas those of Saturn-like complex 2⊃C60 were limited due to the rigidity of the macroring of 2.
DOI: 10.1021/jacs.5b00291
PubMed: 25699988
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Cojal González</name></author><author><name sortKey="Hasegawa, Masashi" sort="Hasegawa, Masashi" uniqKey="Hasegawa M" first="Masashi" last="Hasegawa">Masashi Hasegawa</name><affiliation wicri:level="1"><nlm:affiliation>§Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>§Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373</wicri:regionArea><wicri:noRegion>Kanagawa 252-0373</wicri:noRegion></affiliation></author><author><name sortKey="Nishinaga, Tohru" sort="Nishinaga, Tohru" uniqKey="Nishinaga T" first="Tohru" last="Nishinaga">Tohru Nishinaga</name><affiliation wicri:level="1"><nlm:affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Haque, Tahmina" sort="Haque, Tahmina" uniqKey="Haque T" first="Tahmina" last="Haque">Tahmina Haque</name><affiliation wicri:level="1"><nlm:affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Takase, Masayoshi" sort="Takase, Masayoshi" uniqKey="Takase M" first="Masayoshi" last="Takase">Masayoshi Takase</name><affiliation wicri:level="1"><nlm:affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Otani, Hiroyuki" sort="Otani, Hiroyuki" uniqKey="Otani H" first="Hiroyuki" last="Otani">Hiroyuki Otani</name><affiliation wicri:level="1"><nlm:affiliation>∥Graduate School of Environment and Information Sciences, Yokohama National University, Hodogaya-ku, Yokohama, Kanagawa 240-8501, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>∥Graduate School of Environment and Information Sciences, Yokohama National University, Hodogaya-ku, Yokohama, Kanagawa 240-8501</wicri:regionArea><wicri:noRegion>Kanagawa 240-8501</wicri:noRegion></affiliation></author><author><name sortKey="Rabe, Jurgen P" sort="Rabe, Jurgen P" uniqKey="Rabe J" first="Jürgen P" last="Rabe">Jürgen P. Rabe</name></author><author><name sortKey="Iyoda, Masahiko" sort="Iyoda, Masahiko" uniqKey="Iyoda M" first="Masahiko" last="Iyoda">Masahiko Iyoda</name><affiliation wicri:level="1"><nlm:affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="eISSN">1520-5126</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Two isomers of a multifunctional π-expanded macrocyclic oligothiophene 8-mer, E,E-1 and Z,Z-1, were synthesized using a McMurry coupling of a dialdehyde composed of four 2,5-thienylene and three ethynylene units under high dilution conditions. On the other hand, cyclo[8](2,5-thienylene-ethynylene) 2 was synthesized by intramolecular Sonogashira cyclization of ethynyl bromide 5. From STM measurements, both E,E-1 and Z,Z-1 formed self-assembled monolayers at the solid-liquid interface to produce porous networks, and from X-ray analyses of E,E-1 and 2, both compounds had a round shape with a honeycomb stacked structure. E,E-1 formed various fibrous polymorphs due to nanophase separation of the macrorings. E,E-1 and Z,Z-1 in solution exhibited photochromism upon irradiation with visible and UV light, respectively, and this photoisomerization was confirmed by using STM. Furthermore, amorphous films of Z,Z-1 and E,E-1 showed photoisomerization, although single crystals, fibers, and square tubes of E,E-1 remained unchanged under similar conditions. E,E-1 with a 12.5-14.7 Å inner cavity incorporated fullerene C60 in the cavity in solution and the solid state to produce a Saturn-like complex, whose structure was determined by X-ray analysis. 2 also formed a Saturn-like complex with C60 in the solid state. These Saturn-like complexes are stabilized by van der Waals interactions between the sulfur atoms of 8-mer and C60. The complexes exhibited charge-transfer interactions in the solid state. Like E,E-1, Saturn-like complex E,E-1⊃C60 formed small cube and fiber structures depending on the solvent used, whereas those of Saturn-like complex 2⊃C60 were limited due to the rigidity of the macroring of 2. </div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">25699988</PMID><DateCompleted><Year>2015</Year><Month>08</Month><Day>10</Day></DateCompleted><DateRevised><Year>2015</Year><Month>03</Month><Day>25</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5126</ISSN><JournalIssue CitedMedium="Internet"><Volume>137</Volume><Issue>11</Issue><PubDate><Year>2015</Year><Month>Mar</Month><Day>25</Day></PubDate></JournalIssue><Title>Journal of the American Chemical Society</Title><ISOAbbreviation>J. Am. Chem. Soc.</ISOAbbreviation></Journal><ArticleTitle>Synthesis, structures, and photophysical properties of π-expanded oligothiophene 8-mers and their Saturn-like C₆₀ complexes.</ArticleTitle><Pagination><MedlinePgn>3877-85</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jacs.5b00291</ELocationID><Abstract><AbstractText>Two isomers of a multifunctional π-expanded macrocyclic oligothiophene 8-mer, E,E-1 and Z,Z-1, were synthesized using a McMurry coupling of a dialdehyde composed of four 2,5-thienylene and three ethynylene units under high dilution conditions. On the other hand, cyclo[8](2,5-thienylene-ethynylene) 2 was synthesized by intramolecular Sonogashira cyclization of ethynyl bromide 5. From STM measurements, both E,E-1 and Z,Z-1 formed self-assembled monolayers at the solid-liquid interface to produce porous networks, and from X-ray analyses of E,E-1 and 2, both compounds had a round shape with a honeycomb stacked structure. E,E-1 formed various fibrous polymorphs due to nanophase separation of the macrorings. E,E-1 and Z,Z-1 in solution exhibited photochromism upon irradiation with visible and UV light, respectively, and this photoisomerization was confirmed by using STM. Furthermore, amorphous films of Z,Z-1 and E,E-1 showed photoisomerization, although single crystals, fibers, and square tubes of E,E-1 remained unchanged under similar conditions. E,E-1 with a 12.5-14.7 Å inner cavity incorporated fullerene C60 in the cavity in solution and the solid state to produce a Saturn-like complex, whose structure was determined by X-ray analysis. 2 also formed a Saturn-like complex with C60 in the solid state. These Saturn-like complexes are stabilized by van der Waals interactions between the sulfur atoms of 8-mer and C60. The complexes exhibited charge-transfer interactions in the solid state. Like E,E-1, Saturn-like complex E,E-1⊃C60 formed small cube and fiber structures depending on the solvent used, whereas those of Saturn-like complex 2⊃C60 were limited due to the rigidity of the macroring of 2. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Shimizu</LastName><ForeName>Hideyuki</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cojal González</LastName><ForeName>José D</ForeName><Initials>JD</Initials></Author><Author ValidYN="Y"><LastName>Hasegawa</LastName><ForeName>Masashi</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>§Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Nishinaga</LastName><ForeName>Tohru</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Haque</LastName><ForeName>Tahmina</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Takase</LastName><ForeName>Masayoshi</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Otani</LastName><ForeName>Hiroyuki</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>∥Graduate School of Environment and Information Sciences, Yokohama National University, Hodogaya-ku, Yokohama, Kanagawa 240-8501, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rabe</LastName><ForeName>Jürgen P</ForeName><Initials>JP</Initials></Author><Author ValidYN="Y"><LastName>Iyoda</LastName><ForeName>Masahiko</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>†Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>03</Month><Day>10</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Am Chem Soc</MedlineTA><NlmUniqueID>7503056</NlmUniqueID><ISSNLinking>0002-7863</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>2</Month><Day>21</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>2</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>2</Month><Day>24</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25699988</ArticleId><ArticleId IdType="doi">10.1021/jacs.5b00291</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Japon</li></country><region><li>Région de Kantō</li></region><settlement><li>Tokyo</li></settlement></list><tree><noCountry><name sortKey="Cojal Gonzalez, Jose D" sort="Cojal Gonzalez, Jose D" uniqKey="Cojal Gonzalez J" first="José D" last="Cojal González">José D. Cojal González</name><name sortKey="Rabe, Jurgen P" sort="Rabe, Jurgen P" uniqKey="Rabe J" first="Jürgen P" last="Rabe">Jürgen P. Rabe</name></noCountry><country name="Japon"><region name="Région de Kantō"><name sortKey="Shimizu, Hideyuki" sort="Shimizu, Hideyuki" uniqKey="Shimizu H" first="Hideyuki" last="Shimizu">Hideyuki Shimizu</name></region><name sortKey="Haque, Tahmina" sort="Haque, Tahmina" uniqKey="Haque T" first="Tahmina" last="Haque">Tahmina Haque</name><name sortKey="Hasegawa, Masashi" sort="Hasegawa, Masashi" uniqKey="Hasegawa M" first="Masashi" last="Hasegawa">Masashi Hasegawa</name><name sortKey="Iyoda, Masahiko" sort="Iyoda, Masahiko" uniqKey="Iyoda M" first="Masahiko" last="Iyoda">Masahiko Iyoda</name><name sortKey="Nishinaga, Tohru" sort="Nishinaga, Tohru" uniqKey="Nishinaga T" first="Tohru" last="Nishinaga">Tohru Nishinaga</name><name sortKey="Otani, Hiroyuki" sort="Otani, Hiroyuki" uniqKey="Otani H" first="Hiroyuki" last="Otani">Hiroyuki Otani</name><name sortKey="Takase, Masayoshi" sort="Takase, Masayoshi" uniqKey="Takase M" first="Masayoshi" last="Takase">Masayoshi Takase</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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